Tetrahydrofuran → HCID 21498439, compound

HRID 1729943Notes

Reaction equation

HRID 1729943 reaction equation
[CH3:1][NH:2][C:3]1[S:4][C:5]([S:8](Cl)(=[O:10])=[O:9])=[N:6][N:7]=1.O1CCCC1.[CH3:17][NH:18][CH2:19][C:20]1[O:24][CH:23]=[CH:22][CH:21]=1.C(N(CC)CC)C>O>[CH3:1][NH:2][C:3]1[S:4][C:5]([S:8](=[O:10])(=[O:9])[N:18]([CH3:17])[CH2:19][C:20]2[O:24][CH:23]=[CH:22][CH:21]=2)=[N:6][N:7]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 78492N-MethylfurfurylamineHCID 13563611HCID 13563611, compound

Product 1

HCID 21498439HCID 21498439, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 8.4 g. of 2-methylamino-1,3,4-thiadiazole-5-sulfonyl chloride (see Preparation 1) in 100 ml. of tetrahydrofuran, cooled to about 0° C., there was added dropwise 4.4 g. of methylfurfurylamine. After the addition had been completed, 4.1 g. of triethylamine was added to the mixture dropwise and the mixture was then stirred at ambient room temperature overnight. The reaction product mixture was filtered to remove any salt. The filtrate was concentrated to yield an oil. Water was added to the oil. A precipitate formed which was filtered off and dried. The precipitate weighed about 6.2 g. and had a melting point of about 109°-112° C. It was identified as 2-methylamino-5-[N-methyl-N-furfurylsulfamoyl]-1,3,4-thiadiazole. It was used without further purification in the preparation of some of the final products of the invention.

Workup

  1. additionthere was added dropwise 4.4 g
  2. additionAfter the addition
  3. filtrationThe reaction product mixture was filtered
  4. customto remove any salt
  5. concentrationThe filtrate was concentrated
  6. customto yield an oil
  7. customA precipitate formed which
  8. filtrationwas filtered off
  9. customdried
  10. customIt was used without further purification in the preparation of some of the final products of the invention

Sources & evidence

ORD record
ord-2f737b30196742b8b5341176459dfd22
Source dataset
uspto-grants-1976_11
Patent number
US03990881

Reaction notes

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